The invention relates to certain sulfonylurea compounds having a carbocyclic or heterocyclic ring linked indirectly ortho to the sulfonylurea linkage, compositions thereof and a method of their use as herbicides or plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. Nos. 4,127,405 and 4,169,719 disclose herbicidal benzenesulfonylureas.
European patent application (EP-A) No. 83,975, published July 20, 1983, discloses herbicidal benzenesulfonamides of formula ##STR1## wherein Q is selected from various five or six-membered aromatic or partially unsaturated heterocyclic rings containing 2 or 3 heteroatoms selected from O, S or NR.
European patent application (EP-A) No. 85/476, published Aug. 10, 1983, discloses herbicidal benzenesulfonamides of formulae ##STR2## wherein Q is selected from various 5-membered aromatic heterocycles, and their dihydro and tetrahydro analogs, which contain one heteroatom selected from O, S or NR, or Q is a saturated or partially unsaturated 6-membered ring containing one heteroatom selected from O or S; and
Q.sup.1 is a 6-membered aromatic heterocycle containing one to three N atoms. PA1 C is CO, CR.sub.21 R.sub.22 or SO.sub.2. PA1 R.sup.4 is H or C.sub.1 -C.sub.4 alkyl; PA1 A is Y(CH.sub.2).sub.n R.sup.17 or ##STR8## R.sup.17 is a 5-6-membered heterocyclic radical; Y is O, S or a direct bond; and PA1 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl; PA1 R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms; PA1 R.sub.3 is halogen, H, NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms; PA1 A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl; PA1 m is 0 or 1; PA1 E is N or CH; PA1 X is oxygen, sulfur, SO or SO.sub.2 ; and PA1 Q is, in part, a 5- or 6-membered heterocyclic ring or a fused homologue thereof, each linked through a carbon atom to the bridge --X--A.sub.m -- or, if the heterocyclic ring contains nitrogen, is also bound through a nitrogen atom, and which is unsubstituted or mono- to trisubstituted by halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, --NR.sub.15 R.sub.16 or --SO--NR.sub.17 R.sub.18.
South African patent application No. 83/8416, published May 12, 1984, discloses herbicidal benzenesulfonamides of formula ##STR3## wherein A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms.
European patent application No. 116,518, published Aug. 22, 1984, discloses herbicidal sulfonamides of formula ##STR4## wherein X is NR.sub.6 R.sub.7, N(SO.sub.2 R.sub.9).sub.2 or ##STR5## A is CO, SO.sub.2, CONR.sub.23 or CO.sub.2 ; B is C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkenyl; and
U.S. Pat. No. 4,475,944 discloses herbicidal sulfamates, possessing an ortho-heterocyclic ring, such as those of formula ##STR6## wherein W is O, S or NR.sub.1.
European patent application (EP-A) No. 141,777 (Swiss priority 9/9/83, published 6/15/85) discloses herbicidal sulfonamides of formula ##STR7## wherein R.sup.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or CN;
n is 0 or 1.
South African patent application No. 83/0441 (Swiss priority 1/25/82) discloses herbicidal benzenesulfonamides of formula ##STR9## wherein R.sub.1 is H, halogen, NO.sub.2, C.sub.1 -C.sub.4 haloalkyl,